Chlorine → N-Chlorophthalimide

Participants

Reaction Conditions

Reaction Steps

Chlorine gas was added to one liter of methylene chloride for 20 minutes at 0° C. during which time saturation was achieved. Potassium phthalimide (50 grams; 270 mmoles) was added to the chlorine-saturated methylene chloride. Cooling was discontinued, and the mixture was stirred for two hours during which time the mixture warmed to 20° C. The resulting slightly greenish-yellow mixture was evaporated to a slush without filtering, and water was added to the mixture to dissolve the resulting potassium chloride. The total mixture was filtered, and the solid which was collected was washed with water and then with heptane. The solid was vacuum-dried overnight to obtain 46.4 grams (95.% yield) of N-chlorophthalimide.

Provenance & Evidence